Facile access to regio- and stereoselective synthesis of highly functionalized spiro[indoline-3,2'-pyrrolidines] incorporating a pyrene moiety: experimental, photophysical and theoretical approach.

ABSTRACT: The regio- and stereochemical polar [3 + 2] cycloaddition of azomethine ylides, which were generated in situ by the reaction of isatin and sarcosine or benzylamine, with (E)-3-aryl-1-(pyren-1-yl)prop-2-en-1-ones as dipolarophiles, was studied using experimental and theoretical methods. The chemical structures and relative configurations of all products have been fully established by 1D and 2D homonuclear and heteronuclear correlation NMR spectrometry. The effects of the electronic and steric factors of the reactions were discussed. The photophysical properties of the synthesized spiro[indoline-3,2'-pyrrolidin]-2-ones and 5'-phenyl-spiro[indoline-3,2'-pyrrolidin]-2-ones were studied. The mechanism of the reactions was investigated using global and local reactivity indices and

SUBMITTER: Hussein EM 

PROVIDER: S-EPMC9081859 | biostudies-literature | 2018 Jul

REPOSITORIES: biostudies-literature